title: Chemoselective synthesis of tetrasubstituted furans via intramolecular Wittig reactions: mechanism and theoretical analysis.
abstract: An efficient synthesis of tetrasubstituted furans was achieved from the corresponding α,β-unsaturated ketone derivatives, acid chlorides, and Bu3P in the presence of Et3N via a chemoselective intramolecular Wittig reaction as the key step. The presence of an additional electron-withdrawing group in the α-position of Michael acceptors controlled the chemoselectivities of presumable phosphorus ylides in the intramolecular Wittig reactions, and their mechanisms were also investigated by DFT calculations.
authors.affiliation: Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan, ROC.
authors.forename: Yu-Ting
authors.initials: YT
authors.lastname: Lee
authors.forename: Yen-Te
authors.initials: YT
authors.lastname: Lee
authors.forename: Chia-Jui
authors.initials: CJ
authors.lastname: Lee
authors.forename: Chia-Ning
authors.initials: CN
authors.lastname: Sheu
authors.forename: Bo-Yu
authors.initials: BY
authors.lastname: Lin
authors.forename: Jeng-Han
authors.initials: JH
authors.lastname: Wang
authors.forename: Wenwei
authors.initials: W
authors.lastname: Lin
mesh_terms: D005663:Furans / Q000138:chemical synthesis*; D015394:Molecular Structure; D011789:Quantum Theory
chemical_list: D005663:Furans